Chapter 19, Problem 19.13P

Interpretation Introduction

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.